Acylated lactamides



Uni d Sta e 2,700,616 I ACYLA'I'EDV-LACTA MI DES Martin L. Fein, Riverside NIL, William' Ratchford and Edward M Filachione, Philadelphia, Pa., and Charles H. Fisher, New rl e ans,- La., *assignorsn to the United Secretary of Agriculture No lrawiiig. 'Aiiisncaii irfibv'niiei 1951,": t 1 Serial No. 255,724.. t

8 Claims. '(CL: 106-1181 H I, H (Grantedunde'r Title 35, SgCode (1952),sec. 26 6) A; 'non exclusive,irrevocable, royalty-free license in theinvention herein described; for all governmental purposes, throughout the'world, with the power to grant sublicenses for such purposes, ishereby granted to'the Government of the United States of America.

This invention relates to: sponding to one of the general formulae?" ons-on-oo-N z' i wherein (CnI- Ie1i)"" is 1 a" divalent, aliphatic, saturated acyclic hydrocarbon radical, n being an mtegerfrom 2 to '4; A is an alkyl group jhaving-not-more than llcarh nm R. i h w e -qt 11 s QP m fl H E F 74 a. whereint(nHzfi)r n, and A have the same significance as above; R' is a benzyl group or analkylgroup ,having fromA to., 12,;carbon. atoms; R".1s an'alkylgroup having not more than lljcarbon atoms; Oran alkoxy group havingfromd to 12 carbon atoms, or the grouping i wherein R has the same significance is an inte Y ing in the first mentionedjormula is identlcal to all other As in that formulaand each R appearing in the second mentioned formula is ident'icalto all other Rs in-that'formula.-- W

Compounds; corresponding gto'ythe aforesaid general CnIjIZn are obtained in an analogous manner from the corresponding N,N-bis (hydroxalltyl) lactamldes.

Acylated lactamides wherein R 1s analkyl groupand R; is a benzylor, an alkyl group areobtained by reacb ingthe acylating agent containingthe acyl radical of an aliphatic saturated, monocarboxylic acid having from 2 to '12 carbon atoms, with N,N-di-benzyl or N,N-dialkyl lactamide, respectively. Acylated is-benzyl or-an alkyl group and R" s an alkoxy group are obtained by reacting a N,N- dibenzylor N,N-d1alkyl lactarnide, I respectively, with I an ,alkyl chlorocarbonate,

such. as ibutyl, amyl hexyl, ,dodecyl. chlorocarbonate, ior.

States of America as represented, by the acyla'ted lactamides correger from 1 to 8, and wherein each A appear lactamides wherein R.

7. 1x 2 any other 'iclilo'rocarbonate containing from' 4 1a :l2 earbon atoms in the alkyl group". "Acylatedla'ctamide'swhere? 1s Yl-PE l e dR" s he wa i g 9 'T$ 0 ae r w I i :j 3: :1. 'W' are. obtained by reacting .the -N',N-dibenzyltor. ,N- ial kyl .lactamrde, respectively, with the chloride of maloriic, succrmc, glutaric, adipic,'pimelic; subari'c, azelaic; or" sebacic acid. -'-I .15 :j. T h:

The .acylated lactamides-of @this invention possess properties w 1ch render them useful as modifiers or plasticizing agents for synthetic plasticsand compositions con.

taining them.

The following examples illustrateflthe invention:

, with a;;condenser andth'ermometer. The fla'sk:was heated on a steam bathand one GH3 H-C ON(C4Hn)| A one-liter, three-neck, round. bottom flask, containg onemole N,N-dibutyllactamide, g. of dry pyridine and ml. of ether was fitted with a stirrer, thermometer and dropping :funnel containing one half mole of adipyl chloride. v.Theadipyl chloride was then added to the contents of the flask, slowly and with constant stirring, while maintaining the temperature 'below 20-C. by cooling injan ice-water bath. Upon completion of the exothermic rea ctiorithe mixture was stirred at room temperature until the amount 0t pyridine hydrochloride which separated from thesolution ceased to increase, and approximately 100 ml. of water was then added to dissolve the pyridinehydrochloride precipitate. The contents'of the'fla'sk were transferred to a separatory funnel,

Example IV N,N-dibenzyl lactarriideacetate 0 .4011 0 cardamom .PrQQ- round bottom flask fitted.

was then added to- N,N,-bis-(2 1 g. of acetyl This compound was preparedby the procedure of Example II from equimole'cular amounts of Ngl l-dibutyl lac tamide and l'auroyl chloride.

N,N'-dibutyl lactamide' laurate (ne 1.4558; A d

0.9154) was collected at'132" /0003 mm. Example VlII.-N,N-dibutyl lactamide 2.-ethyl hexanoate CHaCHCO-N(C4Ho)z 0-0 0cH(czH5)cH1 0H-CHoH3 This compound was obtained by reacting N,N-dibutyl lactamide with an equimolecular amount of Z-ethyl hexanoic acid chloride following the procedure of Example II.

N,N-dibutyl lactamide 2-ethyl hexanoate (n11 1.4526; d4 0.9280) was collected"at'-14'6- 'C./1.1 mm.

ta-mide and Z-ethylhexanoyl chloride were reacted in ac cordance with the procedure of. Example II;

N-,N-di--2-ethy1 hexyl' lactamide Z-ethyl hexanoate (m1 1.4590; (14 0.9122) was collected at 119- 124 610.03 mm.

This com'poundwas obtained on reacting equimolecular amounts of di-n-octyl lactamide and rr-arnyl chlorocarbonate, using the procedure of Example II.

1.4558; 114 0.9339) Was collected at l30-132 C./0.01

Example XI.--N-2-hydr0xypr0pyl. lactamide di-Z-ethyl hexanoate N l hydroxypropyl lactarnide was reacted with two-molecular equivalents of'2-'ethyl' hexanoyl chloride, essentially as described, inrExample 11x: N-Z-hydroxypropyl lactamide di-Z-ethyl hexanoate (m 1.4532; (14 0.9747) was collected at 124-127 0/002 'mm.

in Example 1', witl1- an equimo Example XlI.-N-2-hydr0xyethyl lactamide di-Z-ethyl I h-exanoate' om-cH-oo-NH-om-omowo-on-om-om-om-orn O-GO-CH-CHz-CHz-CHz-CH: CzHs N-Z-hydroxyethyi laetarriide was racted with 2 molecular equivalents of 2-ethylhexanoyl chloride, essentially as described in Example The acylated lactamides of Examples E,-'II*,-*and'-*IV-XII are compatible with ethyl cellulose, and those of Examples IIV with cellluloset acetate? Film's cast'from solutions containing these synthetic resins and the acylated lactamide in a weight l atiOLQf 11033, were clear, dry,

tough, and flexible.

' The compositibnofl'clairn l'where resin 18 a vinyl chloride-acetate"copolymer andthe 'plas The. productsof Examples: 1;. II, V-VHI', X, and' X11 are suitable plasticizers for vinyl chloride-acetate copolymer chloride-5% acetate)- as evaluated by: a method essentially similar to that of. Kent and ;Weaver,. 1-947,India Rubber World, 115', 813-816. -The. charac'-' teristics ofthe molded. samplesgso obtained are shown 111 the following table:

- PEAS IIGIZER Compound of Exy 3 w ample I II V VI VII VIII X XII Characteristics of plasticlzed material: I

'1 a n s i l e V strength, p. S.-1f. 3,360 3,410 3}.040-3,290.2",740;3,'140 3,020 3,170 Ultimate elongatiorr, perl cent 290 330 400 i 365 350 310 360 '-370. %m0dulus,, l -7; p v p. 5.1 1,290 1,790 1,340 1,400 1,130 1,290 1,390 1,620 Brittle point,

wherein (CnH2 n)- is a divalent, aliphati'e,' saturated acyclic hydrocarbon radicaL-n being aninteger' from 210 atoms; Ris a me'mber selected from the group=-consist-- asabove;'R." isa" member selected fronr'the group consi'sting' of a benzyl group and? an alkyl group having from 4't'o 12 carbon atoms; 'R"-"is-'a 'member selected fi'om-th'e wherein R7 has the same significance as above and ,x is an integer from 1' to- 8, and wherein the first mentioned formula is identical to each other A 7 in.that formula and each 'R f appearing in the second merrtiori e d formula identical to each other R" in that'for mu a." I

"1;"he. eomposit'ionof-clairn I""where'in"the synthetic reslnis a vinyl;ch1oride acetatefcopolymeri n' the synthetic synthetic resin selected from the group consistingo'f' a vinyl chloride-acetate ccthan 11' carboneach A appearing in.

ticizer therefor is N,N-bis(2-hydroxyethyl) lactamide tripropionate.

4. The composition of claim 1 wherein the synthetic resin is a vinyl chloride-acetate copolymer and the plasticizer therefor is N,N-dibutyllactamide adipate.

5. The composition of claim 1 wherein the synthetic resin is a vinyl chloride-acetate copolymer and the plasticizer therefor is N,N-di-n-octyl lactamide n-amyl carbonate.

6. The composition of claim 1 wherein the synthetic resin is a vinyl chloride-acetate copolymer and the plasticizer therefor is N-Z-hydroxyethyl lactamide di-2-ethyl hexanoate.

7. The composition of claim 1 wherein the synthetic resin is cellulose acetate.

8. The composition of claim 1 wherein the synthetic References Cited in the file of this patent UNITED STATES PATENTS 2,170,845 Woodhouse Aug. 29, 1939 2,290,881 Katzman July 28, 1942 2,399,479 Emerson Apr. 30, 1946 10 2,415,356 Kellogg et al. Feb. 4, 1947 2,531,406 DAlelio Nov. 28, 1950 OTHER REFERENCES Ratchford, Ind. Engineering Chemistry 42, 1565-7 15 (1950).

Ratchford, J. Amer. Chem. Soc. 71, 647-51 (1949). 

1. A COMPOSITION COMPRISING A SYNTHETIC RESIN SELECTED FROM THE GROUP CONSISTING OF A VINYL CHLORIDE-ACETATE COPOLYMER, ETHYL CELLULOSE, AND CELLULOSE ACETATE AND, AS A PHASTICIZER THEREFOR, AN ACYLATED LACTAMIDE CORRESPONDING TO ONE SELECTED FROM THE GROUP CONSISTING OF THE FOLLOWING FORMULAE: 